Questions and Answers
What is the outcome of hydrolyzing esters?
What do amides yield upon hydrolysis?
Which process is known as saponification?
Which method is primarily used to reduce amides?
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What is the primary reactant in the hydrolysis of esters?
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Which statement is true about ester hydrolysis?
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What are the products of ester hydrolysis in basic conditions?
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When amides are hydrolyzed, what happens to the amino group?
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What is typically required to hydrolyze an amide?
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In ester hydrolysis, what role does water play?
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Study Notes
Amines
- Amines are organic derivatives of ammonia, containing a nitrogen atom with a lone pair of electrons, making them both basic and nucleophilic.
- Amines can be classified as primary (1°), secondary (2°), or tertiary (3°) based on the number of alkyl (or aryl) substituents bonded to the nitrogen atom.
Nomenclature of Amines
- Amines with more than one functional group are named by considering the –NH2 as an amino substituent on the parent molecule.
- Amines can be named using the "N-alkyl" term(s) at the beginning of the name.
- Cyclic amides are called lactams.
- Nitriles are named by adding the nitrile suffix to the name of the corresponding alkane.
Properties of Amines
- Amines with fewer than five carbon atoms are generally water-soluble.
- Primary and secondary amines form hydrogen bonds and are highly associated.
- Amines have a distinctive odour, with low-molecular-weight amines having a fishlike aroma.
Substitution of the Hydroxyl Group
- Reactions involving the replacement of the hydroxyl group of a carboxylic acid with another nucleophilic group are important for preparing functional derivatives of carboxylic acids.
Preparation of Amides and Esters
- Acyl halides can be prepared by treating carboxylic acids with thionyl chloride (SOCl2) or phosphorus tribromide (PBr3).
- Acid anhydrides are derived from two molecules of carboxylic acid and amines.
- Amides are usually prepared by reaction of an acid chloride with an amine.
- Esters are prepared by reaction of an acid with an alcohol.
Reactions of Esters and Amides
- Esters undergo hydrolysis to yield carboxylic acids plus alcohols.
- Amides undergo hydrolysis to yield carboxylic acids plus amine on heating in either aqueous acid or aqueous base.
- Amides can also undergo reduction to yield amines.
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Description
Understand the chemistry of amines, their properties, and reactions involving substitution of the hydroxyl group in carboxylic acids.
